Handling a Flirty Boss: Advice from a Hollywood Veteran

When Gretchen Carlson filed a sexual harassment lawsuit against former Fox News boss, Roger Ailes, a “floodgate of harassment allegations” came pouring in from at least a dozen other women with similar claims against the television executive.

What did the stories have in common? They all came from young women seeking to advance their careers when confronted with sexual advances from Ailes in his capacity as a boss, hiring manager and influential media executive. According to NY Mag, he told victims: “You know if you want to play with the big boys, you have to lay with the big boys” and “You know no girls get a job here unless they’re cooperative.”

While the accusations against Ailes report egregious misconduct, not all workplace harassment is this overt. Even subtle flirtatious advances from a supervisor – such as persistent compliments on how “beautiful” you are or ill-concealed favoritism – can place you in a tenuous position at work. When a boss makes a pass at you, it unfairly influences your reputation with colleagues and may even damage your job advancement prospects.

To touch base on office advances, ENTITY talked to Blair Cahill, a former Hollywood production designer, who is all too familiar with unwanted flirtation in the workplace.

Photo Coursesy of Blair Cahill.

“I once worked for a director that pursued me for years,” Cahill recalls. “He would often send production assistants to ask me out and would openly comment on my looks to the entire crew.”

This position could have landed Cahill in two very different positions depending on how she handled the situation.

“I spent my career negotiating these situations – never saying yes and never saying no in the politest way manageable. However, if I had made the decision to go out with him, my career would have most definitely suffered.”

While studies show that generations have become increasingly relaxed on office-dating culture (84 percent of millennials would engage in an office relationship compared to 36 percent of Gen Xers and 29 percent of Boomers), what about the aftermath, be it consensual or not?

According to the lens of Cahill’s experience, “Once the [male pursuer] grows bored with the relationship, the woman was almost always fired and her reputation was ruined. If a woman were to say no outright and damage the male’s ego, her reputation was also damaged and she was accused of ‘not being a team player.’”

If your boss comes on to you in a way that is not mutual, according to Cahill, being polite and diplomatic can save your reputation and career.

“When dealing with unwanted advances, I have learned to always be polite, even if it’s painful – [but] say no firmly.”

If you do feel uncomfortable in a one-on-one meeting, Cahill recommends “to take an assistant or coworker” to meetings with men that you find “to be sexually aggressive.”

When being firm, yet diplomatic, is unsuccessful and you find yourself in a physically and psychologically threatening situation, there are organizations, such as your company’s HR department, that were created to handle sexual harassment cases and to protect you. Organizations like the U.S. Equal Employment Opportunity Commission serve sexual harassment cases if your HR department is unable to act on your situation. Filing a complaint, putting things in writing and being persistent can help you keep your job and your reputation.

While Cahill remembers that “there [were] no human resources departments or any ramifications for inappropriate behavior” during her time working as a production designer in Hollywood, society has progressed, allowing for their implementation.

Sexual harassment cases can range from Gretchen Carlson’s lawsuit against Roger Ailes to a director pursuing Blair Cahill publically at work. Cahill asserts that harassment can be the “hardest challenge” women face in the workplace.

These best way to combat it? Cahill advises, “Being diplomatic is the key.”

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